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Chemical nomenclature, replete as it is with compounds with complex names, is a repository for some names that may be considered unusual. A browse through the Physical Constants of Organic Compounds in the CRC Handbook of Chemistry and Physics (a fundamental resource) will reveal not just the whimsical work of chemists, but the sometimes peculiar compound names that occur as the consequence of simple juxtaposition. Some names derive legitimately from their chemical makeup, from the geographic region where they may be found, the plant or animal species from which they are isolated or the name of the discoverer.
Some are given intentionally unusual trivial names based on their structure, a notable property or at the whim of those who first isolate them. However, many trivial names predate formal naming conventions. Trivial names can also be ambiguous or carry different meanings in different industries, geographic regions and languages.
Godly noted that "Trivial names having the status of INN or ISO are carefully tailor-made for their field of use and are internationally accepted".[1] In his preface to Chemical Nomenclature, Thurlow wrote that "Chemical names do not have to be deadly serious".[2] A website in existence since 1997[3] and maintained at the University of Bristol lists a selection of "molecules with silly or unusual names" strictly for entertainment. These so-called silly or funny trivial names (of course depending on culture) can also serve an educational purpose. In an article in the Journal of Chemical Education, Dennis Ryan argues that students of organic nomenclature (considered a "dry and boring" subject) may actually take an interest in it when tasked with the job of converting funny-sounding chemical trivial names to their proper systematic names.[4]
The collection listed below presents a sample of trivial names and gives an idea how chemists are inspired when they coin a brand new name for a chemical compound outside of systematic naming. It also includes some examples of systematic names and acronyms that accidentally resemble English words.
Glenn Seaborg told his students that he proposed the chemical symbol Pu (from P U) instead of the conventional "Pl" for plutonium as a joke, only to find it officially adopted.[5]
Unununium (Uuu) was the former temporary name of the chemical element number 111, a synthetic transuranium element. This element was named roentgenium (Rg) in November 2004.
A class of compounds with a "window pane motif" (the name fenestrane derives from the Latin word fenestra, meaning window), comprising four fusedcarbocycles centred on a quaternary carbon resulting a twice over spiro compound. The illustration at right shows a generic fenestrane as well as the specific examples [4,4,4,4]fenestrane and [5,5,5,5]fenestrane. Fenestranes are of considerable interest in theoretical chemistry though comparatively few have actually been synthesised.
Also called the buckyball, this is an allotrope of carbon named after Richard Buckminister Fuller due to its resemblance to Fuller's geodesic domes. The term was coined by Harold Kroto.[10] The alternative name footballene was coined by A.D.J. Haymet[11] because the molecule also resembles a football;[3] the 70-atom version is said to resemble a rugby ball from its own oval shape.
(tricyclo[3.3.2.02,8]deca-3,6,9-triene) (C10H10), was named by organic chemistMaitland Jones Jr. for William "Bull" Doering who predicted its properties in 1963.[12][13] Within a specific temperature range the molecule is subject to rapid degenerate Cope rearrangements with the result that all carbon atoms and hydrogen atoms are equivalent and that none of the carbon–carbon bonds is permanent.
(Al2Si2O5(OH)4), a clay-like material with a number of manufacturing uses, one of which is as a coating for high-quality bond paper. It is named after its discoverer, Allan Brugh Dick.[14]
(C4H5As), an analogue of pyrrole in which an arsenicatom replaces the nitrogen atom.[18] The aromaticity of arsoles has been debated for many years.[19] The compound in which a benzene ring is fused to arsole — typically on the carbon atoms 3 and 4 — is known as benzarsole.[3]
Bastardane
A close relative to tetramantane (a higher homologue of adamantane), its proper name is nonacyclo[11.7.1.112,18.03,16.04,13.05,10.06,14.07,11.015,20]docosane. Because its unusual ethano-bridge was a deviation from the standard hydrocarbon caged rearrangements, it came to be known as bastardane—the unwanted child.[3][20]
A class of asymmetric ligands for asymmetric synthesis. The name DuPhos is derived from the chemical company that developed this type of ligand (DuP, DuPont) and the compound class of phospholanes (Phos) it belongs to.
[2-(14-hydroxypentadecyl)-4-methyl-5-oxo-2,5-dihydrofuran-3-carboxylic acid], an aliphaticacid derived from the Australian Xanthoparmelialichen.[3][27]
dUMP
Deoxyuridine monophosphate, an intermediate in nucleotide metabolism
Name sounds like a combination of English words related to recreational drugs: bong; crack, a preparation of cocaine; and acid, a street name for lysergic acid diethylamide.
[37][38] Is also named after an animal, a goat (Hircus).
Or per-iodic acid, is pronounced /ˌpɜːraɪˈɒdɪk/PURR-eye-OD-ik and not */ˌpɪəriˈɒdɪk/PEER-ee-OD-ik. It refers to one of two interconvertible species: HIO4 (metaperiodic acid), or H5IO6 (orthoperiodic acid – illustrated at right). The per- prefix in the name denotes that iodine is present in its highest possible (+VII) oxidation state.
(5,10,15,20-tetrakis(alpha,alpha,alpha-2-pivalamidophenyl)porphyrin), used to model hemeenzyme active sites.
A strongly oxidizing mixture of hydrogen peroxide and sulfuric acid used to remove organic residues from substrates and glassware. The name refers to the voracious appetite of the Amazonian piranha fish.
Rednose
A sugar derived from the degradation of rudolphomycin.[16]
A pheromone of the female American cockroach. Named after the scientific name of this species, Periplaneta americana, not because of periplanarity.[citation needed]
Thebacon
Dihydrocodeinone enol acetate, an opioid analgesic or antitussive.[citation needed]
Dioxygen difluoride, O2F2, an extremely unstable compound which reacts explosively with most other substances – the nickname "FOOF" is a play on its formula.[41]
^Zimmerman, Howard E.; Robert M. Paufler (1960). "Bicyclo [2.2.2]octa-2,5,7-triene (barrelene), a unique cyclic six electron pi system". Journal of the American Chemical Society. 82 (6): 1514–1515. doi:10.1021/ja01491a071.
^Verbrugge, P. A. (1977). "Unusual organic compounds. XXIV. Compounds with the formula (CH)n. (d). Synthesis of cubane, (CH)8; homocubanes". Chemie en Techniek (Amsterdam). 32 (4): 120–123.
^Haymet, A.D.J. (1986). "Footballene: a theoretical prediction for the stable, truncated icosahedral molecule C60". J. Am. Chem. Soc. 108 (2): 319. doi:10.1021/ja00262a035.
^Doering, W. von E.; Roth, W. R. (1963). "A Rapidly Reversible Degenerate Cope Rearrangement : Bicyclo[5.1.0]octa-2,5-diene". Tetrahedron. 19 (5): 715–737. doi:10.1016/S0040-4020(01)99207-5.[dead link]
^Ault, Addison (2001). "The Bullvalene Story. The Conception of Bullvalene, a Molecule That Has No Permanent Structure". J. Chem. Educ.78 (7): 924. Bibcode:2001JChEd..78..924A. doi:10.1021/ed078p924.
^G. Märkl & H. Hauptmann (1983-06-14). "Untersuchungen zur Chemie der Arsole 1,1-dichlor-1-R-λ5-arsole-1-chlorarsole 2,2′,5,5′-tetraphenyldiarsolyl (Studies on the chemistry of arsoles)". J. Organomet. Chem.248 (3): 269–285. doi:10.1016/S0022-328X(00)98709-6.
^Toma, SH; Uemi, M; Nikolaou, S; Tomazela, DM; Eberlin, MN; Toma, HE (2004). "{trans-1,4-Bis[(4-pyridyl)ethenyl]benzene}(2,2'-bipyridine)ruthenium(II) Complexes and Their Supramolecular Assemblies with β-Cyclodextrin". Inorg Chem. 43 (11): 3521–3527. doi:10.1021/ic0352250. PMID15154817.
^Uri J, Csoban G, Viragh E., Acta Physiol Hung. 1951;2(2):223-8.
^See, for example, Okibe, N; Johnson, DB (2004). "Toxicity of flotation reagents to moderately thermophilic bioleaching microorganisms". Biotechnology Letters. 24 (23): 2011–2016. doi:10.1023/A:1021118915720. S2CID23948075.
^"BARF". ChemSpider. Royal Society of Chemistry. 2013. Retrieved 4 November 2013.
^Chester, DO (1979). "Three New Aliphatic Acids from Lichens of Genus Parmelia (Subgenus Xanthoparmelia )". Australian Journal of Chemistry. 32 (11): 2565. doi:10.1071/CH9792565.
^Nordenström, Björn E. W. (1951). "Effect of cadaverine and lysine on the urinary excretion of piperidine in rabbits". Acta Pharmacologica et Toxicologica. 7 (3): 287–296. doi:10.1111/j.1600-0773.1951.tb02870.x. PMID14856760.
^R A Klein, G P Hazlewood, P Kemp, and R M Dawson, Biochem J. 1979 December 1; 183(3): 691–700.
^Charles O, Coolsaet B (1972). "[Prevention of hemorrhage in prostatic surgery. Apropos of the study of the hemostatic activity in prostatectomy of a new molecule: beta-naphthoquinone monosemicarbazone (Naftazone)]". Annales d'Urologie (in French). 6 (3): 209–212. PMID4562066.
^Curran, Dennis P. (1985). "Tandem radical approach to linear condensed cyclopentanoids. Total synthesis of (.+-.)-hirsutene". Journal of the American Chemical Society. 107 (5): 1448–1449. doi:10.1021/ja00291a077.
^Nozoe, Shigeo (1976). "Isolation, structure and synthesis of hirsutene, a precursor hydrocarbon of coriolin biosynthesis". Tetrahedron Letters. 17 (3): 195–198. doi:10.1016/0040-4039(76)80013-5.
^SM Kupchan, KL Stevens, EA Rohlfing, BR Sickles, AT Sneden, RW Miller, RF Bryan, J. Org. Chem., 43(4) (1978) 586
^Sam Kean (2011), The Disappearing Spoon, Little, Brown, p. 36, ISBN9781446437650
Alex Nickon and Ernest F. Silversmith, "Organic Chemistry, the Name Game: Modern Coined Terms and Their Origins", Pergamon 1987. ISBN0-08-034481-X.
Randall, David (February 1, 2004). "Storyville: Molecular scientists have a word for it". The Independent on Sunday. London, England.(subscription required)
Wallechinsky, David; Wallace, Amy (2005). "24. Molecules and amoebas with funny names". The new book of lists : the original compendium of curious information. New York, N.Y.: Canongate. pp. 203–205. ISBN9781841957197.
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